4-Chloro-6-[[4-(diethoxyphosphoryl)butoxy]amino]-2,5-diformamidopyrimidine → 6-Chloro-9-[4-(diethoxyphosphoryl)butoxy]-2-formamidopurine

HRID 373879Notes

Reaction equation

[Cl:1][C:2]1[C:7]([NH:8][CH:9]=O)=[C:6]([NH:11][O:12][CH2:13][CH2:14][CH2:15][CH2:16][P:17]([O:22][CH2:23][CH3:24])([O:19][CH2:20][CH3:21])=[O:18])[N:5]=[C:4]([NH:25][CH:26]=[O:27])[N:3]=1>C(OC(OCC)OCC)(=O)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:25][CH:26]=[O:27])[N:5]=[C:6]2[C:7]=1[N:8]=[CH:9][N:11]2[O:12][CH2:13][CH2:14][CH2:15][CH2:16][P:17]([O:22][CH2:23][CH3:24])([O:19][CH2:20][CH3:21])=[O:18]

Participants

Conditions

Temperature: 120 °C

Procedure

4-Chloro-6-[[4-(diethoxyphosphoryl)butoxy]amino]-2,5-diformamidopyrimidine (0.330 g, 0.78 mmol) was dissolved in diethoxymethyl acetate (4 ml) and the resulting solution was stirred at 120° C. for 2 hr. The reaction mixture was then allowed to cool and evaporated to dryness. The residue was dissolved in methanol: conc. aq. NH3 solution (9:1, 5 ml) and stirred at 23° C. for 5 min. The solvents were evaporated under vacuum and the product was purified by column chromatography on silica gel (eluted with chloroform: ethanol, 96:4) to yield the title compound (0.225 g, 71%), m.p. 98° C. (acetonitrile). 1H NMR: δH ((CD3)2SO) 1.22 (6H, t, J=7Hz, (OCH2CH3)2), 1.76 (6H, m, CH2CH2CH2P), 3.98 (4H, m, (OCH2CH3)2), 4.43 (2H, t, J=6Hz, NOCH2), 8.8 (1H, s, H-8) 9.36 (1H, br.s, NHCHO), 11.29 (1H, br.s, D2O exchangeable, NHCHO).

Workup

temperatureto cool
customevaporated to dryness
dissolutionThe residue was dissolved in methanol
stirringconc. aq. NH3 solution (9:1, 5 ml) and stirred at 23° C. for 5 min
customThe solvents were evaporated under vacuum
customthe product was purified by column chromatography on silica gel (eluted with chloroform: ethanol, 96:4)

Sources & evidence

ORD record: ord-3cff3e288e4045e396864e4b32ea1afa
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05166198

Reaction notes

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